


Return on Investment

by SaorlaSineag



Category: Supernatural RPF
Genre: 69ing, Multi, Threesome - F/M/M, Vaginal Sex
Language: English
Status: Completed
Published: 2018-10-01
Updated: 2018-10-01
Packaged: 2019-07-21 01:28:03
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,746
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16149668
Author URL: https://archiveofourown.org/users/SaorlaSineag/pseuds/SaorlaSineag
Summary: I felt like a fool. I was holding up a long line at the front desk and I knew that I had forgotten to make the reservation. I was picturing me spending a week in a cheap motel down the road somewhere while all my co-workers were enjoying a luxury resort. I would also miss out on the networking with the upper tier executives of the company who were so important to my career.





	Return on Investment

I could not believe it. The woman behind the front desk told me again, "We are sorry sir, but we have no reservation for you and the hotel is completely booked for the whole week because of the meetings and retreat for a major financial institution." 

"I know!" I said. "I am supposed to attend those meetings and participate in the retreat! Please, help me out here." 

I felt like a fool. I was holding up a long line at the front desk and I knew that I had forgotten to make the reservation. I was picturing me spending a week in a cheap motel down the road somewhere while all my co-workers were enjoying a luxury resort. I would also miss out on the networking with the upper tier executives of the company who were so important to my career. 

I had been through the same drill with the woman behind the desk several times and I was really starting to believe that she had no room for me. 

Then, I heard a familiar voice behind me say, "If this young man doesn't mind sharing a suite, put him in one of my extra rooms in the penthouse." 

I turned and saw Jensen Ackles, the famous hedge fund manager who was going to be the keynote speaker at the company meeting. He stuck out his hand and introduced himself and said, "I have enough room in my suite for an army and I wouldn't mind a little company in between golf and a little work if you don't mind sharing a room." 

I was stunned. Ackles was a financial superstar. He had made billions by his mid-20s. He was the darling of the financial television networks because he was tall, handsome, smart and charming in a down home pleasant sort of way. He was raised in Austin, Texas, but was educated at MIT and Harvard. He was probably asked to be the keynote speaker as a way to get a chance to talk to him about our bank providing some kind of services to his hedge fund. 

I stumbled and stammered and managed to finally say, "My name is Jared Padalecki. I appreciate your offer, Mr. Ackles. I desperately need a place to stay. Are you sure it is not too much of an inconvenience for you?" 

Ackles said, "First, call me Jensen. Second, I have stayed in this place before and this suite is so ridiculously big, we may not see each other for days." 

So, Ackles slapped me on the back and said, "Come on, Jared. I will show you your new home for the week." 

Jensen turned to a gorgeous blond girl who could have been a model and said, "Cassie, will you make sure Jared's bags get up to the suite? Thanks a lot." 

Cassie smiled and said, "Sure, Jensen." 

On the elevator ride to the penthouse, Jensen said, "You probably think that Cassie is employed by me because she is drop dead gorgeous and can suck a cock better than any porn star." 

I didn't know what to say other than she was very pretty. 

Jensen laughed and said, "Cassie is gorgeous and she used to suck my cock before she got married, but the truth is that she is a genius and is better at her job than anyone else I could possibly find. She also has a good attitude and will put up with me. She runs my life." 

I was then 22 years old. I was a junior executive at the huge international bank having the retreat at the resort. I was trying to become an investment banker. This was a dream come true to meet Jensen Ackles. 

We were at a luxury Florida resort and top executives from around the word had gathered to meet and play for a week at company expense. I was a former college football player and I sometimes wondered if I was invited to these retreats because I was a scratch golfer. 

I am about 6 feet 4 inches tall and was a very fit 175 pounds. I had lost about twenty pounds since college when I was a wide receiver and running back. I have long chestnut hair. 

Jensen showed me around the penthouse. It was huge. It had a huge living room, a full kitchen, several bedrooms and baths in addition to the master bedroom and bath which were beautiful and gigantic. He gave me one of the extra rooms and told me to make myself at home. 

Jensen opened a bottle of red wine and poured me a glass. I had never tasted anything like it. Jensen laughed when I asked him about it and said that he did not concern himself with stuff like what wine to buy. He left that to Cassie. 

Jensen said he was going to clean up and would see me in a few minutes. I heard the shower running while I drank a second glass of the superb wine. I truly could not believe how good it tasted. 

Cassie came into the suite a few minutes later. She asked me if everything was okay for me and I told her that everything was great. She then asked, "Does Jensen still have his clothes on?" 

I gave her a perplexed look and said, "He did the last time I saw him, but he is taking a shower now. Why did you ask?" 

Cassie smiled and said, "I just wanted to warn you that Jensen spends a lot of time when he is not working in the nude. He doesn't care who sees him. It throws some people off." 

I told her, "If I can stay in this suite and drink this wine, I don't care what Jensen wants to wear around his suite. He doesn't go nude in front of you, does he?" 

"Oh, yeah. All of the time. But, I have seen it all before and I have an understanding husband. The huge paycheck Jensen gives me helps my husband be understanding." 

Cassie asked me about my job and I asked about her husband and her interesting job. I really liked her, and I could quickly see that she was very bright and very charming. Cassie said that since Jensen had taken me in, I needed to understand that everything that goes on around the suite this week is confidential and cannot be revealed to anyone including my bosses. 

Cassie said that one of her main jobs was to avoid securities law violations. She laughed and said that she also had to protect Jensen from the gossip magazines to the extent that was possible. Jensen was constantly seen with super models and beautiful young actresses. The gossip magazines could not resist a handsome billionaire with a super model. 

Cassie laughed and said she felt like a pimp keeping track of all of Jensen's women. I told her that from what I had seen in the papers she was doing a good job. 

About that time, Jensen came back into the living room. He was naked and was drying his hair with a big white towel. Jensen looked great. He was muscular and tan. He obviously worked out a lot. He also had a partial erection and the biggest cock I had ever seen hanging down between his legs. 

I had seen a lot of naked guys in locker rooms over the years and I had never paid much attention to their bodies. For some reason, I became instantly aroused by Jensen's body, especially his big cock. It was huge and thick, and it looked great swinging between his legs as he slowly walked in drying his hair. I was literally weak in the knees. I felt like I might fall down. I also was somewhat embarrassed that I instantly had an erection. This had never happened to me from looking at a man. 

Of course, lovely Cassie was seeing the same thing I was. I found it exciting that Jensen was showing his big dick to this beautiful girl.  

However, this was apparently old hat to Cassie. She said to Jensen, "You are walking around with an erection in front of your guest! Can you cover that thing up, please?" 

Jensen laughed and said, "Oh, Cassie. You have been doing that to guys for years. Maybe you could help me out with this erection." 

Cassie rolled her eyes and said, "You didn't even know I was here. And, you know I don't want to help you with your erection problem." 

Jensen laughed. "Too bad you had to get married!" 

Cassie said, "I have good news for your erection problem. Alberta is flying in to see you on her way to New York. I am just guessing that she knows what to do about an erection." 

Jensen smiled and said, "Great! Jared, you will enjoy meeting Dani, she is a lingerie and bathing suit model from L.A." 

I was confused. "Who is Alberta?" 

Jensen laughed and said, "Alberta Einstein is Cassie’s nickname for Dani. Cassie does not think that Dani is too bright. That may be true, but she has other redeeming qualities." 

Cassie turned to me and said, " Dani’s redeeming qualities all fit in a double D bra. She actually thought that Florida was between Los Angeles and New York." 

Jensen smiled and said, "Now, Cassie, it may be more complicated than you think to get those big tits in those tiny lace bras." 

Cassie laughed and said, "I still think that 'Alberta Einstein' is appropriate. She is coming to see you because she does not understand basic geography." 

I was not used to having discussions with a man who is naked and has a huge semi-hard cock. I kept trying to avoid staring at his cock. I think he may have noticed that I was looking at his long, thick cock. Cassie did not seem to care that Jensen was showing her his cock. 

Cassie and Jensen talked business privately for 15 or 20 minutes and then Jensen rejoined me and the wine. He opened a new bottle and we talked for a while. 

We talked about our workout routines, sports, women and investing. I told Jensen I was working 70- or 80-hour weeks in one of the Texas offices of the bank. He laughed and said, "I know you have to do that to get your opportunity to be a lead investment banker, but I do okay investing and work less than a couple of hours a day most of the time." 

I was stunned to hear that. I thought hedge fund managers worked constantly. 

Jensen said, "Don't tell anyone, but the way I invest, I make a few very hard decisions and then wait very patiently to see if we make money. I have found that I can be much more patient if my cock is in someone's mouth or I am playing a sport. Staring at a computer screen is boring and makes me want to do something to relieve the boredom. I make more money when I am patient." 

It all sounded good to me. 

Jensen showed me photos of the girl who was coming to visit him. The pictures were spectacularly sexy. Dani had huge tits that appeared to be natural and was extremely skinny. She was blonde and beautiful. Jensen said that if I wanted, I could have sex with her too.  

Jensen said, "Dani loves sex and she will fuck a good-looking guy like you if I ask her nicely. Come to think of it, it would be fun if she fucked us both at the same time." 

My head was spinning from the fact that I was in a huge penthouse that must cost thousands per night with a guy I admired greatly drinking great wine. Now, I was being offered group sex with a beautiful lingerie model.  

I knew I should say no, but instead, I said, "Why don't we let Dani decide." 

I figured that Dani would only want to have sex with Jensen since she was flying across the country to see him. 

Jensen said, "Great!" 

We drank and talked some more. I was amazed at how open and unreserved Jensen was with me. It seemed like he would say most anything to me and was never embarrassed about it. He was extremely self confident and sure of himself. I guess that happens when you are tall, handsome, smart, rich and hung. 

Late in the afternoon Dani arrived at the penthouse. She was prettier in person than she was in the internet photos. Her face and hair were perfect, her body was fabulous, and she was dressed in tight pants with sexy high heels. As advertised, her tits were almost too big to be real, yet they looked real and moved like real tits every time she took a step. 

Dani gave Jensen a kiss and shook my hand. 

Jensen said, "Dani, this is my friend, Jared. As you can see, he has a nice, muscular body. I thought it would be fun if Jared and I fucked you at the same time." 

I expected Dani to object, but instead I heard, "Wow! That will be fun, Jensen. Do you want to do it here or the bedroom?" 

"You two take your clothes off and head for the bedroom," Jensen said. 

I couldn't believe this gorgeous girl was so willing to do whatever Jensen suggested, but I did not see how I could gracefully decline at that point and did not want to. 

I pulled off my clothes and looked up to see Dani release her giant tits. It was a spectacular sight to see her boobs bounce as she unhooked her sexy black lace bra. My cock was hard immediately. 

Jensen said, "Dani, look at that nice cock Jared has for you. It is big too. What is it Jared, 10 inches?" 

"9 and a half," I said. 

Dani said, "Man, this is going to be fun!" 

I was relieved at her reaction because I was a little self-conscious about how much smaller my cock was than Jensen’s. 

Jensen threw down his towel and revealed his cock that was longer and thicker than mine even though it wasn't fully hard yet.  

Jensen directed traffic in the bedroom. He had me lay on my back on the big bed in the middle. He positioned my body just the way he wanted by moving me around. Then, he had Dani get in the 69 position on top of me. My cock was instantly in her mouth and it felt great. I started licking away at her pussy and squeezed her giant tits. The tits were definitely real. 

Jensen provided encouragement to both Dani and me. He was on his knees beside us as Dani sucked my cock. Occasionally, Jensen would stick his big cock in Dani's face and she would suck it for a while before she came back to mine. 

Dani was moaning and squealing. Jensen was beside us talking dirty to Dani and encouraging her to suck my dick harder and take it deeper. 

Dani could definitely suck a cock. I felt like I was on the verge of cumming in her pretty mouth. She was obviously enjoying having her pussy licked. 

Then, Jensen joined the activities in earnest. He came around behind Dani on his knees. His big cock was hard and was just above my head as I licked her. I was concentrating on Dani’s lips on my cock when the head of Jensen's huge cock appeared in front of my face and entered Dani’s pussy. At first, only a little of Jensen's cock was in her pussy, but she was moaning and reacting to the big cock.  

I had never been so close to a man's cock. It was just an inch or two above my face. I was extremely turned on and started to lick her clit even more enthusiastically. I was afraid I was going to lick Jensen's cock and was afraid it might offend him. 

I stopped licking for a moment and said, "Jensen, do you want me to move?" 

Both Jensen and Dani told me to keep licking her pussy. 

So, I had a close up view of a monster cock fucking a beautiful girl. Every time the giant cock would enter very far into Dani, she would shudder and moan. I watched the cock go deeper and deeper into the pussy. 

Finally, after a long while, Jensen rammed it all the way in. Dani completely lost it and moaned loudly with my cock still in her mouth. I felt her cum as Jensen fucked her. I wanted to lick the big cock, but I was afraid of grossing out Jensen, so I just licked Dani's clit and from time to time felt Jensen's big cock hit my face as he fucked her. 

I was so excited that a moment after she started to orgasm, I exploded into her mouth. Jensen continued to pound away at Dani for a while and I think she came again. 

Finally, Jensen buried his big cock deep into her and came in her pussy. I was hard again from watching it happen right in front of me. For a few minutes, Jensen and Dani had their weight on my face. Then, Jackson slowly pulled his cock out of her and his big cock covered in cum and Dani's juices slowly slid across my forehead leaving a wet trail on my forehead and in my hair. 

I had just cum, but I was totally horny and ready for more. I had never experienced anything nearly as hot as sex with Dani and Jensen. Jensen smiled as he watched me wipe his cum off of my forehead.  

I did not want to admit it even to myself, but I loved the idea of Jensen's cock right in my face.  

Jensen had dinner sent up to the suite and we all had dinner and more wine. After dinner, Dani had to rush to catch her plane to New York. She gave us each a kiss and was gone. 

Jensen and I continued to drink red wine and talk. Jensen had a way of getting people to talk about things they would never normally discuss. For example, he asked me what kind of porn I like to watch. For some reason, I told him I like porn involving girls giving blow jobs, submissive girls and dirty talking.  

The next thing I know, he had me searching for this kind of porn on his laptop. Soon, Jensen was naked sitting next to me watching porn movies I had found. Jensen encouraged me to get naked too. I declined. 

After a few more glasses of wine, Jensen started to rub his big cock as he watched the movies. I had never seen a guy beat off in front of me. I was embarrassed, but I was also fascinated by his enormous prick. It had to be 10 or 11 inches long and it was thick. 

"Jensen, how long is that thing?" I asked. 

"I don't know." he replied. "I will call Cassie for a tape measure." 

I tried to discourage a call to Cassie, but Jensen called immediately. 

Cassie appeared 15 minutes later with a tape measure.  

Jensen said, "Jared wants to measure my cock. You may want to leave before he does it." 

I tried to protest, but Jensen was off to the rest room before I could correct him. 

Cassie asked, "Jared, are you bisexual?" 

"No." I said. 

"Jensen is and he is very persuasive. You better watch out." Cassie warned. 

I wasn't sure I was completely against being persuaded and I was very interested to hear that Jensen was bisexual. But, to Cassie I said, "Thanks for the warning. I will be careful, but it shouldn't be too hard to resist since I am not gay." 

Cassie just smiled and said, "Okay, but I used to say that I would never have sex with my boss before Jensen persuaded me to have sex with him. I didn't even know I was being seduced." 

Cassie left, and Jensen came back with the tape measure. He said, "Jared, you want to help me get my cock hard before you measure it?" 

I laughed and declined. 

Jensen then handed me the tape measure and started jerking his cock. I was sitting next to him as he stroked his big cock. It seemed bigger than ever. I didn't understand why, but I was excited to look at the big monster. 

After a few minutes, Jensen told me to measure it. I tried to resist, but Jensen told me that just measuring his dick was not gay. So, I pulled out the tape and measured his hard cock. 

It was truly magnificent. I had to touch it and sort of hold it as I measured. It was thick and heavy. I took my time with the measurement. I could feel Jensen staring at me as I touched his cock. 

The measurement showed that Jensen's cock was 11 inches long and was 7 inches around. I had to hold his cock in my hand for the measurement of the thickness. It was the first time I had ever touched a cock other than my own. 

Jensen teased me about measuring it with my mouth, but I politely declined. I screwed up when I declined though because I said, "I am not ready for that!" 

It was supposed to be a joke of some sort, but it sounded like I might be ready for it soon. 

We kept drinking and talking. Jensen returned to the porn on his laptop. He asked, "Have you ever watched Gay porn, Jared?" 

I said, "Yes." 

"Do you like it, Jared?" 

"Yes, but I have never said that to anyone." 

Jensen said, "I won't tell. Do you like the movies where the Guy has a big cock or the movies where the Guy has a little cock?" 

I couldn't believe I was having this conversation, but I was drunk enough to say, "I like the ones where the Guy has a huge cock." I really did, and I really did not know why. I was able to just compartmentalize it in my mind and not think about it very often. 

Jensen looked me in the eye and said, "I bet you fantasize about sucking on a Guy’s huge cock." 

-FIN-


End file.
